Cycloaddition approach to new potential lead molecules based on the arylethyl amine theme

ORGN 909

Daniel Blanco Ania, d.blancoania@science.ru.nl1, Carolina Valderas Cortina, martirio03@yahoo.es1, Floris P. J. T. Rutjes1, Hans W. Scheeren, h.scheeren@science.ru.nl1, Floris L. van Delft1, Leo A. J. M. Sliedregt2, Bart van Steen2, and Pedro H. H. Hermkens3. (1) Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, Nijmegen, 6525 ED, Netherlands, (2) Chemical Design & Synthesis, Solvay Pharmaceuticals, CJ van Houtenlaan 36, Weesp, 1380 A, Netherlands, (3) N. V. Organon, Oss, 5340 BH, Netherlands
The arylethyl amine moiety is a key structural element in neurotransmitters and central nervous system (CNS) active drugs. Their activity partially depends on the conformation of this particular moiety. We wish to report a short and versatile synthesis of skeletally diverse libraries of potentially CNS active molecules, ranging from spiro- to tetracyclic structures, all containing a rigidified arylethyl amine moiety as a core feature. The synthesis starts from nitro and cyano acetates and includes a 1,3-dipolar cycloaddition reaction as the key step. The resulting scaffolds have been further functionalized in a parallel fashion.

 

Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 AM-12:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 132, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006